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I've attempted a similar strategy with my latest league. I'm playing out every game, and using 12-13 relievers instead of the traditional setup. I haven't gone as deep as you have, but I do tend to try and start weaker players, then bringing in the stronger pitchers to handle the heart of the lineup.
It's a fictional league, so I was able to draft an amazing offense before getting my staff. One thing I messed up a bit on was stamina - most of my guys are under 20 in stamina, so I have to carry 13 pitchers, and 12 hitters - backup catcher, IF, and OF (my DH is also an OF), and the IF and OF have to be able to play all positions.
Lots of success so far, though - 32-16, including a 10-1 stretch where my staff has a sub-3 era (in a league where the average is 5-ish), and the only loss was after an extra inning game where my tired staff gave up 16.
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